Overview for MACiE Entry M0187
EC Number: 220.127.116.11 (A member of the Isomerases, Racemases and epimerases, Acting on hydroxy acids and derivatives)
Enzyme Name: mandelate racemase
Biological Species: Pseudomonas putida (Bacteria)
Catalytic Chain UniprotKB Accession Codes:
Representative PDB Code: 1mns - ON THE ROLE OF LYSINE 166 IN THE MECHANISM OF MANDELATE RACEMASE FROM PSEUDOMONAS PUTIDA: MECHANISTIC AND CRYSTALLOGRAPHIC EVIDENCE FORSTEREOSPECIFIC ALKYLATION BY (R)-ALPHA-PHENYLGLYCIDATE (Resolution = 2.00 Å).
Catalytic CATH Codes:
"Other" CATH Codes:
Display structure information
Overall Comment: The mechanism shown in the following steps refers to the direction shown in overall reaction not in the reverse direction. Lys166 is the (S)-specific acid/base catalyst and His297 is the (R)-specific acid/base catalyst, thus in the reverse reaction, His297 deprotonates the (R)-mandelate and the intermediate is reprotonated from Lys166.
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Stepwise Description of the Reaction
|Step 1||Lys166 deprotonates the (S)-mandelate substrate, which results in a keto-enol tautomerisation.|
|Step 2||The intermediate undergoes another keto-enol tautomerisation which reprotonates the intermediate from His297.|
|Step 3||His297 deprotonates water, which deprotonates Lys166 in an inferred return step.|
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Catalytic Residues Involved
||Location of Function
Metal Cofactors for M0187
- J. A. Gerlt et al. (1993), J. Am. Chem. Soc., 115, 11552-11568. An explanation for rapid enzyme-catalyzed proton abstraction from carbon acids: importance of late transition states in concerted mechanisms.
- S. L. Schafer et al. (1996), Biochemistry, 35, 5662-5669. Mechanism of the reaction catalyzed by mandelate racemase: structure and mechanistic properties of the D270N mutant.
- M. Garcia-Viloca et al. (2001), J. Am. Chem. Soc., 123, 709-721. A QM/MM study of the racemization of vinylglycolate catalyzed by mandelate racemase enzyme.
Homologue information for M0187 (1mns)
MACiE Homologues (within the PDB)
MACiE Homologues (within UniprotKB/SwissProt)
Entries with at least one Catalytic CATH code in common (different mechanisms):
|M0311 ||phosphopyruvate hydratase |
|M0269 ||muconate cycloisomerase |
View a comparison of the other reactions in MACiE with the CATH domain 18.104.22.168
View a comparison of the other reactions in MACiE with the CATH domain 3.30.390.10
Links to this entry in other databases